4,8-Dichloroquinoline → Methyl 2-(8-chloro-4-quinolinylamino)-5-fluoro-benzoate

HRID 224595

반응식

HRID 224595 반응식
Cl[C:2]1[C:11]2[C:6](=[C:7]([Cl:12])[CH:8]=[CH:9][CH:10]=2)[N:5]=[CH:4][CH:3]=1.[NH2:13][C:14]1[CH:23]=[CH:22][C:21]([F:24])=[CH:20][C:15]=1[C:16]([O:18][CH3:19])=[O:17]>Cl>[Cl:12][C:7]1[CH:8]=[CH:9][CH:10]=[C:11]2[C:6]=1[N:5]=[CH:4][CH:3]=[C:2]2[NH:13][C:14]1[CH:23]=[CH:22][C:21]([F:24])=[CH:20][C:15]=1[C:16]([O:18][CH3:19])=[O:17]

참가 물질

4

반응물 2

HCID 889734,8-DichloroquinolineHCID 2783401Methyl 2-amino-5-fluorobenzoate

생성물 1

HCID 23331697Methyl 2-(8-chloro-4-quinolinylamino)-5-fluoro-benzoate수율 37.2%

시약·촉매·용매 1

HCID 313Hydrochloric Acid용매

실험 절차

A mixture of 11.88 g of 4,8 dichloroquinoline, 10.4 g of methyl 2-amino-5-fluoro-benzoate and 60 ml of 2 N hydrochloric acid was refluxed for 21/2 hours and was then cooled to ≃0° C. and vacuum filtered. The moist residue was dissolved in 125 ml of lukewarm methanol and triethylamine was added to the resulting solution to make the pH alkaline. The mixture stood overnight at room temperature and was vacuum filtered and the recovered product was washed with water and dried to obtain 8.3 g of raw product which was crystallized from methanol to obtain 7.39 g of methyl 2-(8-chloro-4-quinolinylamino)-5-fluoro-benzoate melting at 196° C.

후처리

  1. temperaturewas refluxed for 21/2 hours
  2. temperaturewas then cooled
  3. customto ≃0° C.
  4. filtrationvacuum filtered
  5. dissolutionThe moist residue was dissolved in 125 ml of lukewarm methanol
  6. additiontriethylamine was added to the resulting solution
  7. filtrationfiltered
  8. washthe recovered product was washed with water
  9. customdried
  10. customto obtain 8.3 g of raw product which
  11. customwas crystallized from methanol

출처 및 근거

ORD 기록
ord-8e8e86e7a4f64221afc1550ed08a30bf
출처 데이터셋
uspto-grants-1980_11
특허 번호
US04233305

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